Holiday rentals in Chipley

A Taste of Farm Life

Have fun with the whole family at this stylish place. Our two-bedroom two bath home located in the country, surrounded by farm fields, barns and cow pasture. Great for vacations! Just an hour from the World's most beautiful beaches, 6 miles south of Graceville, FL, and 7 miles north of Chipley, Fl. There are two queen beds, and a pack-n-play. There is a highchair, children's table and chairs, dining table, bar, bar stools, couch, and loveseat. Washer and dryer provided. No pets or smoking.

Guesthouse & Pool

This family friendly home is less than 2 miles from Walmart and restaurants. Wifi, Netflix, Starz, Prime video are included with your stay. There is one queen bed, one full bed, a queen size sleeper sofa, & a twin. All of which can accommodate a total of 7 guests. Chipley is located off I-10. It is a 55-minute drive to the beach and a 45-minute drive to Dothan, AL. Falling Waters State Park is 3 miles away. Caverns park 15 miles. No pets & no smoking allowed. Home is sanitized between guests.

Come Stay At The Blue House/Entire Home/Stargaze

Escape the hustle and bustle of the city and immerse yourself in the serene embrace of country living at our charming Airbnb retreat. Step outside and be greeted by the crisp, fresh air that fills your lungs with vitality. As night falls, prepare to be captivated by the enchanting spectacle of the night sky with minimal light pollution Whether you're seeking a romantic getaway, a peaceful retreat, or simply a break from the ordinary, our Airbnb listing promises an unforgettable experience.

Lakefront Home+Private Beach+Firepit+Kayaks+Floats

Escape to this serene lakefront house, with your own private white sandy beach, Kayaks, and a firepit with firewood. It's perfect for families, groups of friends, or couples looking to unwind and enjoy nature. Just 30 minutes from gulf beaches & the international airport, and close to spring-fed creeks, recreation areas, horseback riding, fishing, and caves, this property offers a variety of outdoor activities for everyone. We hope you write your own amazing stories in our slice of heaven.

Peaceful Romantic Escape, Pool, Hot Tub, Breakfast

Settle into a private romantic cottage at Camelot, where nothing pulls at you and everything feels easy. Soak together in a clean, perfectly warm hot tub behind a privacy fence, swim in the heated indoor pool, and wake slowly to peaceful country views, friendly farm animals, and hot gourmet breakfast delivered to your door. No rushing, no struggle—just privacy, comfort, and time to reconnect. Add romantic dinners, celebration extras, and resort-like pampering for an unforgettable stay.

Cozy Cottage in the Pines

Enjoy a quiet stay just outside of town on a farm! Listen to the breeze whisper through the pines and relax in this peaceful country setting. The cottage is 2 miles north of Cottonwood and is just under 10 miles to The Ross Clark Circle in Dothan. Dothan has a lot to do…..shopping, dining, and entertainment. Also, the cottage is only a few miles from the Florida line and the Georgia line if you’re going there for something fun! WiFi is fast so working from the cottage is easy as well!

The Bunkie on Wetappo Creek

Enjoy a tranquil getaway in this cozy and comfortable studio cottage overlooking the water. Are you working remotely and looking for the perfect retreat space? A couple looking to leave it all behind for a bit and recharge? Come and enjoy the peaceful sounds of happy birds and whispering pines, all while being a short 15 minute drive away from the Gulf of Mexico and its white sand beaches. This private and peaceful space surrounded by Mother Nature invites you to relax and unwind.

Cozy Barndominium

This quaint barndo leaves nothing to be desired with its charming, rustic interior and modern amenities. New appliances and all the comforts of home are sure to make your stay as pleasant as possible. This is a 1 bedroom 1 bathroom home with two additional twin beds in the loft. This is a smaller space but is very functional and comfortable. Only 50 minutes from Panama City's white sand beaches and 7 minutes from Chipley, it's conveniently located for those wanting to explore.

The Tiny House of Healing - Rustic Rural Edition

Let the honeybees restore what the locusts have taken! Peaceful ranch-style cottage with loft, full kitchen and bath. King bed on main level, queen in loft, plus recliner. Enjoy a swingset, tree swing, board games, and walking trail. Bring the kids and enjoy the outdoors! Located between many springs and caverns. Fresh, crisp well water straight from the tap believe to be the same water that flows into the springs! Come rest, recharge, and breathe deep.

Shady Oaks Cabin on the Hill

Nestled in a serene country setting, this is our guest house up the hill from our country home. The Little White Cabin under the oaks is the perfect retreat for anyone seeking peace, charm, and simplicity. A newly painted facade in crisp white, the cabin’s mint-green door and cozy front porch complete with rocking chairs offer the ideal spot to sip your morning coffee or unwind at sunset. Close to local springs and a short 45 min drive to Panama City Beach.

Chipola Woods quiet & cozy near Caverns, Bear Paw

No cleaning fees! Our one & only peaceful, quiet golf cart friendly location conveniently between I-10/US90 yet the Caverns, Bear Paw river float, Merritts Mill Pond, Hinson Nature Preserve, Blue Springs and all shops, cinema, boat launches & restaurants within a 10 min drive. Golfing, beach, & airports within 1 hour. Modern cottage on a private 1/2 acre equipped with large smart TV's in both the living room and bedroom with Prime video.

Making Memories Lucas Lake

The sun seems to shine brighter on this lovely lakefront home! Ideal for family nature retreats. Enjoy boating, water sports, fishing and kayaking on this 480 acre spring fed lake with 2 boat landings and private dock. Relax on the large deck with dining, lounging and grilling areas; overlooking the spacious back yard with firepit and plenty of room for outdoor games and beautiful lake views.